I upgraded a few years in a row now, basically to take better advantage of newer platform features, even though I stuck with entry-level CPUs.
I went with P35-DS3R boards, with Pentium dual-core (C2D) E2140 CPU, then upgraded to Q9300 CPUs.
Then I bought an AM2+ board with four PCI-E x16 slots for GPU crunching, and four 9600GSO cards.
Then I bought some various X48 boards, which I never really used.
Bought an AM3(+) board, an ASRock 990FX Extreme4, and a Thuban 1045T. Mostly because it had both SATA6G, and lots of PCI-E x16 slots, as well as PCI, and even IDE and floppy. I wanted a versatile "bridge" platform.
I did not invest in Sandy or Ivy Bridge.
When Haswell came around, and they had the (cheap!) H81 boards with G3258 combos for under $100, along with overclocking, I picked a few of those up. (Still buying those for budget "Facebook builds".)
Last year, bought some Skylake ASRock Z170 Pro4S boards, and Pentium G4400 dual-core CPUs, and BLCK OCed them past 4Ghz. FAST! for web browsing. Some of the best single-threaded speed on the market, at any price. Though somewhat hobbled for gaming, being only two cores and no HyperThreading.
A few months ago, I bought an i5-6400 (2.7Ghz stock, BLCK OCed in an ASRock B150 K4/Hyper board to 4.45Ghz), for gaming.
Picked up some 4K UHD TVs as monitors.
Most recently, picked up a Kaby Lake G4600 Pentium dual-core, WITH HyperThreading (that's new for Pentiums), for one of my ASRock DeskMini mini-STX PCs.
Thinking about selling my ATX overclocked gaming boxes. (Maybe.)
Using the DeskMini's more, connected to my HDMI2.0 4K screen using Club3D DP-to-HDMI2.0 adapters, so that I can run @ 4K60, rather than 4K30 off of the native HDMI1.4.
Pretty disappointed that Intel stuck with HDMI1.4 for Kaby Lake too, and didn't implement native HDMI2.0, but there could have been platform-compatibility issues there too, I suppose, since it was going into the same mobo as Skylake.